Tholloside

Details

• Internal ID: e2e9e749-9051-4ef7-a625-ccec03405036
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5S,8R,9S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C4C(CCC3(C2)O)C5(CCC(C5(CC4O)C)C6=CC(=O)OC6)O)C=O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)C=O)O)O)O
• InChI: InChI=1S/C29H42O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)21-18(4-7-28(27,36)10-16)29(37)8-5-17(15-9-20(32)38-12-15)26(29,2)11-19(21)31/h9,13-14,16-19,21-25,31,33-37H,3-8,10-12H2,1-2H3/t14-,16-,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28-,29-/m0/s1
• InChI Key: AZOXLPPOBHVORY-DMUQYFGMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₁₁
• Molecular Weight: 566.60 g/mol
• Exact Mass: 566.27271215 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -0.28
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• Thollosid
• Toloside
• 6875-30-5
• Thollosid [German]
• Sarmentosigenin-L-rhamnosid
• Sarmentosigenin-L-rhamnosid [German]
• AKOS040754195
• 19-Oxo-3-beta-((L-rhamnopyranosyl)oxy)-5,11-alpha,14-trihydroxy-5-beta-card-20(22)-enolide
• 5-beta-Card-20(22)-enolide, 3-beta-((L-rhamnopyranosyl)oxy)-5,11-alpha,14-trihydroxy-19-oxo-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9049	90.49%
Caco-2	-	0.8664	86.64%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8685	86.85%
OATP2B1 inhibitior	-	0.7473	74.73%
OATP1B1 inhibitior	+	0.9406	94.06%
OATP1B3 inhibitior	+	0.9699	96.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6084	60.84%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5098	50.98%
CYP3A4 substrate	+	0.7097	70.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8978	89.78%
CYP3A4 inhibition	-	0.9010	90.10%
CYP2C9 inhibition	-	0.9147	91.47%
CYP2C19 inhibition	-	0.9441	94.41%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.9305	93.05%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9472	94.72%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5635	56.35%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9422	94.22%
Skin irritation	-	0.5151	51.51%
Skin corrosion	-	0.9270	92.70%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8267	82.67%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7268	72.68%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8092	80.92%
Acute Oral Toxicity (c)	I	0.8450	84.50%
Estrogen receptor binding	+	0.8535	85.35%
Androgen receptor binding	+	0.8218	82.18%
Thyroid receptor binding	-	0.5713	57.13%
Glucocorticoid receptor binding	+	0.6098	60.98%
Aromatase binding	+	0.7180	71.80%
PPAR gamma	+	0.5348	53.48%
Honey bee toxicity	-	0.7297	72.97%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9827	98.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.42%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.08%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.53%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.42%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.12%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.19%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.17%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.52%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.88%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.61%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.43%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.12%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.77%	95.89%
CHEMBL4208	P20618	Proteasome component C5	87.01%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.58%	92.94%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.11%	83.57%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.31%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	84.85%	95.93%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.36%	91.38%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.62%	94.78%

Plants that contains it

• Convallaria majalis
• Ornithogalum nutans

Cross-Links

• PubChem: 101694273
• LOTUS: LTS0185527
• wikiData: Q104921841